The Real Frank Tassone and the True Story Behind HBO's 'Bad Education'

Leena Kim
Photo credit: JoJo Whilden
Photo credit: JoJo Whilden

From Town & Country

Over the weekend, HBO released Bad Education, a Hugh Jackman-led film about a real life school scandal that took place nearly two decades ago in an affluent suburb of Long Island. Jackman plays Frank Tassone, a successful, charismatic superintendent of the Roslyn School District in Roslyn, New York, who goes on to steal $11.2 million from the school budget with his associate Pamela Gluckin (played by Oscar winner Allison Janney) in the largest public school embezzlement in U.S. history.

Director Cory Finley created the dramatized retelling of the spectacular 2002 scandal with the help of screenwriter Mike Makowsky, who was a middle schooler in Roslyn when all of this was happening. Here is everything we know about the real life events behind Bad Education.

Who Is Frank Tassone?

Photo credit: Newsday LLC
Photo credit: Newsday LLC

To the students, parents, and teachers of Roslyn, Frank Tassone was a charming and eloquent school administrator with a doctorate degree from Columbia University who regularly ate lunch with students, led a book group with school parents, and kept a photo of his late wife on his desk.

As they would all eventually find out, Tassone was actually leading a double life, stealing millions in taxpayer money ($2.2 million to be exact) to finance the Park Avenue apartment he shared with his partner Stephen Signorelli (or Thomas Tuggiero in the film), the trips to Las Vegas to visit his lover Jason Daugherty (aka Kyle Contreras in the movie), plus the expensive suits, cars, and cosmetic surgeries, along with the more idiosyncratic expenses, such as $37,385 in dry cleaning bills, $5,236 for Christmas cards, and $56,000 to a diet doctor.

He Turned Roslyn High Into One of America's Best Schools

Tassone was, however, an effective superintendent. During his 12-year tenure, Roslyn High School, which is located in Long Island's tony North Shore just over 20 miles outside of Manhattan (former Roslyn residents include the late fashion designer Lilly Pulitzer and Billions co-creator Brian Koppelman) entered the top ten in national rankings of the best public schools.

A month before Tassone's crimes were exposed in May 2004, the Wall Street Journal ranked Roslyn the sixth-best public high school in America. According to the New York magazine story that inspired the HBO flick, "A diploma from Roslyn High School is the closest you can get on Long Island to a ticket to Harvard."

Who Was Pamela Gluckin?

Photo credit: Courtesy of HBO
Photo credit: Courtesy of HBO

Gluckin was the assistant superintendent and business administrator of the Roslyn School District. When the school board found out she was using the district credit card for personal expenses to the tune of $250,000, Tassone—in order to conceal his own crimes—promptly threw Gluckin under the bus, forcing her to resign and lose her license.

Of course it would later be revealed that Gluckin stole much more than $250,000. The actual sum was $4.3 million, which she used for Florida and Hamptons vacation homes, jewelry, art, and other purchases. Her niece Debra Rigano (in the film her character's name is Jenny Aquila), who worked as a district clerk, was also in on the scheme and was accused of stealing more than $780,000.

Gluckin's son John McCormick (his name is Jimmy McCarden in the movie), whose immense Home Depot shopping spree with the district credit card is what got his mother in trouble in the first place, ended up serving five years of probation and 100 hours of community service for the $83,000 he stole.

In an act of self-preservation, Tassone convinced the school board not to go to the authorities regarding Gluckin's six-figure theft, arguing it would affect Roslyn's reputation and school ranking.

Tassone's Eventual Downfall Was Precipitated by a School Reporter

Photo credit: Courtesy of HBO
Photo credit: Courtesy of HBO

In the movie, a student reporter named Rachel Bhargava (played by Geraldine Viswanathan) is working on a story about a new school construction project for Roslyn High's school newspaper, The Hilltop Beacon, and begins to dig deeper into the school's financial records to eventually uncover Tassone's multimillion-dollar embezzlement.

In real life, Tassone's unraveling did come at the hands of a student reporter, Rebekahn Rombom, but via different means. Rombom got a tip about the real reason behind Gluckin's firing and her story led to authorities and major news outlets catching on to their years-long con.

Is Bob Spicer Based on a Real Person?

Photo credit: Courtesy of HBO
Photo credit: Courtesy of HBO

The short answer is no. Ray Romano plays Bob Spicer, a real estate agent and head of the school board, who, like the rest of Roslyn's overachieving, education-obsessed parents, is thrilled with—and consequently blinded by—Tassano's successes in raising the school's test scores and Ivy League admissions, which in turn made real estate prices soar and cemented Roslyn's status as the most sought-after zip code on Long Island. "In real estate, especially on Long Island, a town is only as good as its public school system," he says. While Spicer is not based on a real-life individual, he's meant to represent the Roslyn community.

Where Is Frank Tassone Now?

Photo credit: Newsday LLC
Photo credit: Newsday LLC

In 2006, Tassone was sentenced to four to 12 years in prison for larceny but got out early, in 2010, for good behavior and was put on probation until 2018. The now-septuagenarian is forbidden from holding any job that requires handling money. He currently lives a low-profile life in New York but still receives a generous pension of $170,000 a year (the result of an oversight in state pension law).

This month, he was a guest on personal life coach Mike Bayer's podcast, where he spoke about finding out last fall that a movie was to be made about his crime. "I just crumbled," he said. "I thought this finally was over. You know, it'll never be over for me, because every day I feel pain."

Where Is Pamela Gluckin Now?

Gluckin, who was sentenced to three to nine years, was released in 2011 and remained on parole until 2015. It was reported that she vowed to contribute half her pension ($55,000 annually) every year to repay the Roslyn school district and found a job working at a nonprofit in Queens. She died in 2017.

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